Hydrochloric Acid → 3-Cyano-4-(2-methylphenyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

HRID 1013309노트

반응식

HRID 1013309 반응식
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:5]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:4]=1[C:33]([O:35]C)=[O:34])#[N:2].[OH-].[Na+].Cl>O1CCCC1.CO>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:5]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:4]=1[C:33]([OH:35])=[O:34])#[N:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67315489Methyl 3-cyano-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

생성물 1

HCID 673154113-Cyano-4-(2-methylphenyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of EXAMPLE 133A (16 mg) and sodium hydroxide (200 μl) in tetrahydrofuran (0.5 ml) and methanol (0.5 ml) was stirred overnight, neutralized with diluted HCl, and concentrated. The residue was purified by RPHPLC to provide the desired product. 1H NMR (500 MHz, dimethyl sulfoxide-d6) δ 14.24 (s, 1H), 8.14 (d, J=8.54 Hz, 1H), 7.86 (dd, J=7.48, 5.65 Hz, 2H), 7.35-7.61 (m, 5H), 7.18-7.36 (m, 3H), 7.12 (d, J=7.32 Hz, 1H), 7.06 (d, J=7.02 Hz, 1H), 6.89 (d, J=7.32 Hz, 1H), 4.77-5.18 (m, 2H), 4.24 (t, J=5.03 Hz, 2H), 2.30-2.47 (m, 2H), 1.99 (s, 3H).

후처리

  1. concentrationconcentrated
  2. customThe residue was purified by RPHPLC

출처 및 근거

ORD 기록
ord-d0295556b8ac46bcb39b987525f61475
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981888B2

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